When facing an IRS audit, appeal, Tax Court case, or collection matter, most taxpayers focus exclusively on the facts and figures of their case. But here’s something that might surprise you: your attitude and approach during IRS interactions can shape your outcome just as much as the merits of your case.
As a former IRS agent turned tax attorney, I’ve been on both sides of the table countless times. I can tell you from experience that how you approach these interactions makes a massive difference in the results you get.
In this article, I’ll share four behavioral principles drawn from classic books on communication and influence—principles I’ve seen work in real tax cases to help taxpayers achieve better outcomes with the IRS.
Why Your Approach Matters in IRS Disputes
I know what you might be thinking: “The IRS is impossible to deal with. I sit on hold forever. The agents are strict and don’t believe me. Why does my attitude even matter?”
The reality is that IRS agents are people doing their jobs within a massive government bureaucracy. While the system itself can be frustrating—with long wait times, bureaucratic red tape, and complex procedures—the individual agent sitting across from you didn’t create these problems.
When you understand this distinction and adjust your approach accordingly, you open doors that might otherwise remain closed. Let’s explore the four principles that can help you do exactly that.
Principle 1: Begin in a Friendly Way
This principle comes from Dale Carnegie’s timeless classic How to Win Friends and Influence People. Carnegie shares an Abraham Lincoln quote that perfectly captures this idea: “A drop of honey catches more flies than a gallon of gall.”
The Aesop’s Fable That Explains Everything
Carnegie illustrates this principle with Aesop’s fable of the North Wind and the Sun. In the story, the North Wind and the Sun argue about who is stronger. When a traveler walks by wearing a coat, they make a bet: whoever can make the traveler remove his coat will be deemed the strongest.
The North Wind goes first, blowing hard and fierce. But the harder the wind blows, the tighter the traveler wraps his coat around himself. The traveler resists with increasing determination.
Then the Sun takes a different approach. It simply shines warmly. Within minutes, the traveler voluntarily removes his coat.
Application to IRS Audits
When you walk into an IRS audit or other interaction acting angry and combative, you’re being like the North Wind. You’re making the agent defensive, and they’re going to hold onto their position even tighter.
But when you start friendly and cooperative, you’re the Sun. You create an environment where the agent actually wants to work with you.
Important caveat: I’m not saying you should be a pushover. There’s absolutely a time to be firm with the IRS. But nothing will hurt your tax case faster than getting into arguments with the IRS agent right from the start.
Principle 2: Seek First to Understand, Then to Be Understood
This principle comes from Stephen Covey’s influential book The 7 Habits of Highly Effective People, and it’s all about empathetic listening.
The Listening Problem Most of Us Have
I’m guilty of this myself: listening to reply instead of listening to understand. As soon as I think I know where the conversation is going, I’m already preparing my response in my head.
Here’s a simple example. Imagine you’re at a restaurant and a server asks, “Are you enjoying your meal?” You might quickly say “It’s delicious” without fully listening. But what if the full question was: “Are you enjoying your meal, because the kitchen wanted me to let you know that dish was accidentally made with nuts, in case you have any allergies”?
If you have a nut allergy, that completely changes your response, right?
How This Applies to IRS Interactions
The same thing happens in IRS interactions. You need to fully listen and understand what the agent is actually saying before you formulate your reply. Don’t be afraid to take it slow and ask clarifying questions. If you’re worried about forgetting your points, write them down while you continue to listen.
The Second Half: Being Understood
The second part of Covey’s principle—”then to be understood”—is about skillfully conveying your position. Many IRS employees are used to people getting agitated or taking hard, combative stances immediately.
When I was an IRS agent, the most successful communications happened when taxpayers explained their position thoroughly and calmly. Remember this common legal phrase: “Reasonable minds can differ.”
The agent might not have all the facts or might have a different perspective. Your job is to help them understand your point of view in a civil manner, not to attack them.
Principle 3: Treat the IRS Agent the Way You’d Want to Be Treated
This is the Golden Rule, which comes straight from the Bible: “Do to others as you would have them do to you.”
What I Learned as an IRS Agent
I’ve been on both sides of the audit table many times. Here’s what I learned as an IRS agent: most people’s frustrations with the IRS have nothing to do with the individual employee sitting across from them.
Yes, the IRS can be incredibly frustrating:
- Long phone wait times
- Bureaucratic red tape
- The inconvenience of an audit
All of that is real, and I’m not minimizing it. But those problems aren’t caused by the agent in the room with you.
Remember: Agents Are People Too
That agent is just a person doing their job:
- They didn’t create the tax code (Congress did that)
- They didn’t personally decide to audit you (the IRS selection system did that)
- They’re working within a massive government system with its own rules and constraints
When you take out your frustrations with the system on the individual agent, you’re essentially shooting yourself in the foot. Keep your perspective and treat that agent with basic human respect.
I’ve consistently found that audits and other IRS interactions turn out better when you follow this simple principle.
Principle 4: Strategic Transparency—Acknowledge the Weaknesses of Your Case
This principle may seem counterintuitive, but it’s incredibly powerful. It comes from Chris Voss’s book Never Split the Difference, where the former FBI hostage negotiator recommends doing what he calls an “accusation audit” before any high-stakes negotiation.
This applies perfectly to IRS situations.
How the Accusation Audit Works
Before you meet with the IRS or talk with an agent, list every negative thing they could possibly say about your case:
- Every accusation they could make
- Every weakness in your position
- Every potential counterargument
For example, if you’re arguing for penalty abatement because you filed late, the IRS might say:
- “Didn’t you know you had a filing responsibility?”
- “Wasn’t it unreasonable to rely on your accountant without confirming they filed your return?”
Here’s the key: YOU bring up these weaknesses first, before the IRS can use them against you.
Why Does This Work?
Strategic transparency works because it:
- Demonstrates self-awareness and honesty
- Shows you have nothing to hide
- Reduces the agent’s suspicion
- Helps build rapport with the agent
Real Case Example: Harry’s Six-Figure Refund
Let me share an example from my own practice. I had a client—let’s call him Harry—who was trying to get a six-figure refund from an amended return. His CPA had initially filed the return incorrectly, sending the loss back to the wrong year. Then the CPA filed a corrected version but sent it to the wrong IRS address.
Here’s the problem: under tax law, a return is only considered filed on time if it’s addressed correctly. So the IRS denied the refund.
When I filed an appeal protesting the IRS’s denial, I didn’t hide this mistake. I acknowledged right up front that the CPA had mailed the return to the wrong address. But then I argued that Harry shouldn’t be penalized for his CPA’s error.
I also pointed out that the IRS had actually processed the original incorrect amended return sent to that same wrong address—proving they received it and accepted it.
The result? A few months later, Harry got his full refund check for hundreds of thousands of dollars. No additional meetings required. No further arguments necessary.
Acknowledging that weakness first, combined with proper context and explanation, made all the difference in Harry’s case.
The Bottom Line: Attitude Matters in IRS Disputes
Many taxpayers think acting tough will help their IRS case, but I’ve seen where that leads—and it’s often nowhere good.
Back when I was a revenue agent, one of my colleagues had a case get so bad that two armed agents with shotguns had to deliver the final paperwork to the taxpayer. I’ll let you guess what was in that paperwork. It wasn’t a refund check.
The Reality About IRS Interactions
Dealing with the IRS is as much about mindset as it is about facts and figures. The way you approach an interaction can either open doors or slam them shut.
If you’re combative and angry:
- You raise red flags
- You make the agent defensive
- You close off possibilities for resolution
But if you’re polite, professional, and strategic:
- The agent is more likely to take you at your word
- They’re more likely to work with you toward a reasonable outcome
- You create opportunities for better results
Four Principles, Proven Results
These four principles I’ve shared with you aren’t just nice ideas or hypotheticals:
- Begin in a friendly way (be the Sun, not the North Wind)
- Seek first to understand, then to be understood (practice empathetic listening)
- Treat the IRS agent with respect (follow the Golden Rule)
- Be strategically transparent (acknowledge weaknesses first)
They’re practical tools that can genuinely improve your IRS outcome, and I’ve seen them work repeatedly in my own practice.
When You Need Professional Help With the IRS
If you’re facing an IRS audit, appeal, Tax Court case, or collection issue and want help navigating it the right way, that’s exactly what we do at Boss Tax Law.
As a former IRS agent, CPA, and tax attorney admitted to practice in all three federal tax courts, Andrew Bosserman specializes in representing business owners and high net worth individuals in disputes with the IRS. Contact Boss Tax Law today to get strategic insight into your IRS dispute.